When your start-up takes off and your team grows, it is tempting to delegate everything you can. However, as you navigate your company's further growth, you should be careful not to let go of your ability to do things yourself. For me, finding opportunities to stay engaged in day-to-day operations has been an important element of my leadership style. As they say, the best form of management is to lead by doing.
I had a recent reminder at CarGurus of how important leading by doing is when we launched a new product and sales strategy. To be sure, we were barking up the right tree, and to better understand where we were in the process, I got personally involved with the initiative.
My decision to take on a handful of new prospective accounts in the sales process had a tremendous effect. It was invigorating for me, it challenged the sales team (shouldn't they be better at this than I am?), and it showed my employees that I'm not afraid to get down to business in any part of the company.
Did I close every lead? Certainly not, but I cultivated a few new client relationships, learned more about customer interest in the product, and was able to close one deal on my own. Experiencing the sales cycle firsthand also gave me the insight I needed to better communicate with the sales team.
I saw the same behavior at my last company, TripAdvisor. My co-founder and current CEO of TripAdvisor, Stephen Kaufer, was notorious for emailing developers in the middle of the night with specific problems he found with the product. Yes, it put our developers on notice that their code was under close scrutiny. But the more important message was that the CEO took it upon himself to check the quality of the product; that mentality permeated the organization.
At CarGurus, I love seeing our management team walk the walk. Our VP of engineering is a great example. When recently asked about our running a new feature on the site, he dove right in and coded up the feature on his own, getting it completed by the end of that same day. He could have easily delegated the task to his team of engineers, but his curiosity and desire to move fast led him to do the work himself. He wanted to learn and believed the experience would allow him to better manage other projects down the line.
When I was still at TripAdvisor as chairman and co-founder, someone at another company once tried to schedule a meeting with me. At this point, we were already one of the top five most trafficked travel websites in the world and had a large employee base. The person on the phone asked me to give them the name and phone number of my executive assistant. My response? "You're talking to him..." I'm proud to say that in the many years I was at TripAdvisor, nobody in the company had an executive assistant.
To run a company, you of course need to delegate, but pick your spots and continue to roll up your sleeves and get dirty. You'll see the entire organization follow that lead.